TWI423980B - 苯并氧氮呯ｐｉ３ｋ抑制劑化合物及使用方法 - Google Patents

Info

Publication number

TWI423980B

TWI423980B TW099132661A TW99132661A TWI423980B TW I423980 B TWI423980 B TW I423980B TW 099132661 A TW099132661 A TW 099132661A TW 99132661 A TW99132661 A TW 99132661A TW I423980 B TWI423980 B TW I423980B

Authority

TW

Taiwan

Prior art keywords

alkyl

alkylene

group

mmol

etoac

Prior art date

2009-09-28

Links

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• 150000001875 compounds Chemical class 0.000 title claims description 295
• 238000000034 method Methods 0.000 title description 79
• 239000012828 PI3K inhibitor Substances 0.000 title description 6
• 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 title description 6
• ZCXLTWVZYXBHJS-UHFFFAOYSA-N 1,2-benzoxazepine Chemical compound O1N=CC=CC2=CC=CC=C12 ZCXLTWVZYXBHJS-UHFFFAOYSA-N 0.000 title description 2
• -1 alkylene R 10 Chemical compound 0.000 claims description 171
• 229910052739 hydrogen Inorganic materials 0.000 claims description 158
• 125000000217 alkyl group Chemical group 0.000 claims description 113
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 105
• 125000002947 alkylene group Chemical group 0.000 claims description 104
• 125000000623 heterocyclic group Chemical group 0.000 claims description 94
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 77
• 125000001072 heteroaryl group Chemical group 0.000 claims description 67
• 229910052801 chlorine Inorganic materials 0.000 claims description 40
• 229910052731 fluorine Inorganic materials 0.000 claims description 39
• 125000003118 aryl group Chemical group 0.000 claims description 37
• 229910052794 bromium Inorganic materials 0.000 claims description 37
• 238000011282 treatment Methods 0.000 claims description 37
• 229910052740 iodine Inorganic materials 0.000 claims description 36
• 206010028980 Neoplasm Diseases 0.000 claims description 34
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 31
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 30
• 239000001257 hydrogen Substances 0.000 claims description 27
• 229910052757 nitrogen Inorganic materials 0.000 claims description 27
• 150000003839 salts Chemical class 0.000 claims description 26
• 201000011510 cancer Diseases 0.000 claims description 25
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
• 239000003814 drug Substances 0.000 claims description 21
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 20
• 239000008194 pharmaceutical composition Substances 0.000 claims description 20
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 18
• 239000003795 chemical substances by application Substances 0.000 claims description 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 14
• 239000002246 antineoplastic agent Substances 0.000 claims description 13
• 229940127089 cytotoxic agent Drugs 0.000 claims description 12
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
• 229910052799 carbon Inorganic materials 0.000 claims description 11
• 239000003085 diluting agent Substances 0.000 claims description 11
• 125000003342 alkenyl group Chemical group 0.000 claims description 10
• 125000000304 alkynyl group Chemical group 0.000 claims description 10
• 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 9
• 102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 claims description 9
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 9
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 9
• 108091007960 PI3Ks Proteins 0.000 claims description 9
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 150000002431 hydrogen Chemical class 0.000 claims description 8
• 125000002883 imidazolyl group Chemical group 0.000 claims description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
• 125000004193 piperazinyl group Chemical group 0.000 claims description 8
• 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 8
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 7
• 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 7
• 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 claims description 7
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 6
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 6
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
• 125000004076 pyridyl group Chemical group 0.000 claims description 6
• 125000002837 carbocyclic group Chemical group 0.000 claims description 5
• 125000003566 oxetanyl group Chemical group 0.000 claims description 5
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 5
• 229940124597 therapeutic agent Drugs 0.000 claims description 5
• VVZRKVYGKNFTRR-UHFFFAOYSA-N 12h-benzo[a]xanthene Chemical group C1=CC=CC2=C3CC4=CC=CC=C4OC3=CC=C21 VVZRKVYGKNFTRR-UHFFFAOYSA-N 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 3
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 3
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
• 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• 230000001404 mediated effect Effects 0.000 claims description 2
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 2
• XHTUOWXUBNMVEU-UHFFFAOYSA-N 1-benzoyl-5-ethyl-5-(3-methylbutyl)-1,3-diazinane-2,4,6-trione Chemical group O=C1C(CC)(CCC(C)C)C(=O)NC(=O)N1C(=O)C1=CC=CC=C1 XHTUOWXUBNMVEU-UHFFFAOYSA-N 0.000 claims 1
• ZZMMFFFSXXINPH-UHFFFAOYSA-N 2-[4-[2-(2-propan-2-yl-1,2,4-triazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]imidazol-1-yl]ethanol Chemical compound CC(C)N1N=CN=C1C1=CN(CCOC=2C3=CC=C(C=2)C=2N=CN(CCO)C=2)C3=N1 ZZMMFFFSXXINPH-UHFFFAOYSA-N 0.000 claims 1
• 208000019838 Blood disease Diseases 0.000 claims 1
• 208000024172 Cardiovascular disease Diseases 0.000 claims 1
• 208000029462 Immunodeficiency disease Diseases 0.000 claims 1
• 239000002260 anti-inflammatory agent Substances 0.000 claims 1
• 229940121363 anti-inflammatory agent Drugs 0.000 claims 1
• 239000003443 antiviral agent Substances 0.000 claims 1
• 206010012601 diabetes mellitus Diseases 0.000 claims 1
• 208000014951 hematologic disease Diseases 0.000 claims 1
• 208000018706 hematopoietic system disease Diseases 0.000 claims 1
• 150000002460 imidazoles Chemical class 0.000 claims 1
• 239000002955 immunomodulating agent Substances 0.000 claims 1
• 229940121354 immunomodulator Drugs 0.000 claims 1
• 208000019423 liver disease Diseases 0.000 claims 1
• 239000003076 neurotropic agent Substances 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 454
• 239000000203 mixture Substances 0.000 description 227
• 235000019439 ethyl acetate Nutrition 0.000 description 223
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 195
• 239000000243 solution Substances 0.000 description 133
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 132
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 121
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 114
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 94
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 79
• 239000011541 reaction mixture Substances 0.000 description 78
• 238000005481 NMR spectroscopy Methods 0.000 description 77
• 238000006243 chemical reaction Methods 0.000 description 71
• 239000007787 solid Substances 0.000 description 56
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 49
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 49
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
• 239000012267 brine Substances 0.000 description 45
• 238000009472 formulation Methods 0.000 description 42
• 239000000460 chlorine Substances 0.000 description 41
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
• 239000011734 sodium Substances 0.000 description 36
• 239000000725 suspension Substances 0.000 description 34
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 32
• 239000000284 extract Substances 0.000 description 32
• 239000000047 product Substances 0.000 description 32
• 238000003818 flash chromatography Methods 0.000 description 31
• HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 description 27
• 239000002904 solvent Substances 0.000 description 27
• 239000004480 active ingredient Substances 0.000 description 26
• 239000012044 organic layer Substances 0.000 description 25
• 239000002244 precipitate Substances 0.000 description 25
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 23
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
• 229920006395 saturated elastomer Polymers 0.000 description 23
• 229910004298 SiO 2 Inorganic materials 0.000 description 21
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• 201000010099 disease Diseases 0.000 description 21
• 238000002360 preparation method Methods 0.000 description 21
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
• 210000004027 cell Anatomy 0.000 description 19
• OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 19
• 125000004432 carbon atom Chemical group C* 0.000 description 18
• 238000000746 purification Methods 0.000 description 18
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 17
• 241000124008 Mammalia Species 0.000 description 17
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 16
• 230000000694 effects Effects 0.000 description 16
• LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 16
• 239000000463 material Substances 0.000 description 16
• 238000010992 reflux Methods 0.000 description 16
• 238000003756 stirring Methods 0.000 description 16
• DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 15
• 239000003153 chemical reaction reagent Substances 0.000 description 15
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 15
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 15
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 14
• 238000004587 chromatography analysis Methods 0.000 description 14
• 238000010438 heat treatment Methods 0.000 description 14
• 229960000583 acetic acid Drugs 0.000 description 13
• 239000002253 acid Substances 0.000 description 13
• 238000001914 filtration Methods 0.000 description 13
• 239000002207 metabolite Substances 0.000 description 13
• 230000001225 therapeutic effect Effects 0.000 description 13
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• 102000003993 Phosphatidylinositol 3-kinases Human genes 0.000 description 12
• 108090000430 Phosphatidylinositol 3-kinases Proteins 0.000 description 12
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
• 125000004429 atom Chemical group 0.000 description 12
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
• 229940079593 drug Drugs 0.000 description 12
• 230000003463 hyperproliferative effect Effects 0.000 description 12
• 239000003921 oil Substances 0.000 description 12
• 235000019198 oils Nutrition 0.000 description 12
• 125000001424 substituent group Chemical group 0.000 description 12
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 11
• 238000004458 analytical method Methods 0.000 description 11
• 239000007864 aqueous solution Substances 0.000 description 11
• 239000002585 base Substances 0.000 description 11
• 208000035475 disorder Diseases 0.000 description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 10
• 230000002401 inhibitory effect Effects 0.000 description 10
• 239000010410 layer Substances 0.000 description 10
• 239000000126 substance Substances 0.000 description 10
• PDKOLTZINNEJAN-UHFFFAOYSA-N 5-chloro-1-(2,4-difluorophenyl)-1,2,4-triazole Chemical compound FC1=CC(F)=CC=C1N1C(Cl)=NC=N1 PDKOLTZINNEJAN-UHFFFAOYSA-N 0.000 description 9
• 239000012141 concentrate Substances 0.000 description 9
• 235000008504 concentrate Nutrition 0.000 description 9
• 238000001727 in vivo Methods 0.000 description 9
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 9
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
• NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 8
• 150000002148 esters Chemical class 0.000 description 8
• 239000000706 filtrate Substances 0.000 description 8
• 229940015043 glyoxal Drugs 0.000 description 8
• 230000007062 hydrolysis Effects 0.000 description 8
• 238000006460 hydrolysis reaction Methods 0.000 description 8
• 239000012071 phase Substances 0.000 description 8
• SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
• 239000007858 starting material Substances 0.000 description 8
• PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 7
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
• FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 7
• 229910000024 caesium carbonate Inorganic materials 0.000 description 7
• 239000003995 emulsifying agent Substances 0.000 description 7
• 150000002500 ions Chemical class 0.000 description 7
• 239000007788 liquid Substances 0.000 description 7
• 239000007937 lozenge Substances 0.000 description 7
• 150000002825 nitriles Chemical class 0.000 description 7
• 229910000104 sodium hydride Inorganic materials 0.000 description 7
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 6
• 239000004215 Carbon black (E152) Substances 0.000 description 6
• GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 6
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
• 229910021529 ammonia Inorganic materials 0.000 description 6
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical class C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
• 239000000872 buffer Substances 0.000 description 6
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 6
• 229930195733 hydrocarbon Natural products 0.000 description 6
• 238000000338 in vitro Methods 0.000 description 6
• IUYHWZFSGMZEOG-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].C[CH-]C IUYHWZFSGMZEOG-UHFFFAOYSA-M 0.000 description 6
• 230000002503 metabolic effect Effects 0.000 description 6
• 231100000252 nontoxic Toxicity 0.000 description 6
• 230000003000 nontoxic effect Effects 0.000 description 6
• IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 6
• 239000000843 powder Substances 0.000 description 6
• 230000008569 process Effects 0.000 description 6
• 230000002829 reductive effect Effects 0.000 description 6
• 125000006413 ring segment Chemical group 0.000 description 6
• WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 description 6
• 229910052708 sodium Inorganic materials 0.000 description 6
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
• 239000012453 solvate Substances 0.000 description 6
• 239000003381 stabilizer Substances 0.000 description 6
• 229910052717 sulfur Inorganic materials 0.000 description 6
• 239000003826 tablet Substances 0.000 description 6
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 description 5
• KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 5
• BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
• 206010009944 Colon cancer Diseases 0.000 description 5
• 108010010803 Gelatin Proteins 0.000 description 5
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 5
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
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